data_AXA
# 
_chem_comp.id                                    AXA 
_chem_comp.name                                  (5S)-5-(2-amino-2-oxoethyl)-4-oxo-N-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-2-carboxamide 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C22 H21 N5 O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2008-07-06 
_chem_comp.pdbx_modified_date                    2009-02-27 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        467.498 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AXA 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        3DNG 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  PDBJ 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
AXA CAH  CAH  C 0 1 Y N N 9.208  -4.384  31.616 -4.831 0.973  0.647  CAH  AXA 1  
AXA CAY  CAY  C 0 1 Y N N 9.047  -3.050  31.261 -5.934 0.171  0.405  CAY  AXA 2  
AXA N1   N1   N 0 1 N N N 8.855  -2.090  32.261 -6.626 -0.434 1.464  N1   AXA 3  
AXA CAV  CAV  C 0 1 N N N 8.763  -0.746  31.887 -7.483 -1.443 1.193  CAV  AXA 4  
AXA OAC  OAC  O 0 1 N N N 8.549  0.125   32.729 -8.116 -1.961 2.089  OAC  AXA 5  
AXA CAM  CAM  C 0 1 N N N 8.908  -0.425  30.542 -7.651 -1.922 -0.226 CAM  AXA 6  
AXA OAS  OAS  O 0 1 N N N 8.661  -1.426  29.542 -7.452 -0.830 -1.128 OAS  AXA 7  
AXA CAZ  CAZ  C 0 1 Y N N 9.033  -2.680  29.920 -6.368 -0.041 -0.903 CAZ  AXA 8  
AXA CAG  CAG  C 0 1 Y N N 9.226  -3.647  28.938 -5.695 0.552  -1.957 CAG  AXA 9  
AXA CAF  CAF  C 0 1 Y N N 9.402  -4.979  29.294 -4.594 1.352  -1.709 CAF  AXA 10 
AXA CAX  CAX  C 0 1 Y N N 9.386  -5.352  30.634 -4.163 1.561  -0.412 CAX  AXA 11 
AXA CAL  CAL  C 0 1 N N N 9.561  -6.818  31.035 -2.963 2.434  -0.151 CAL  AXA 12 
AXA N2   N2   N 0 1 N N N 9.678  -7.638  29.821 -1.750 1.612  -0.161 N2   AXA 13 
AXA CAW  CAW  C 0 1 N N N 10.834 -7.792  29.181 -0.548 2.182  0.052  CAW  AXA 14 
AXA OAD  OAD  O 0 1 N N N 11.888 -7.245  29.502 -0.469 3.379  0.252  OAD  AXA 15 
AXA CBB  CBB  C 0 1 N N N 10.749 -8.663  27.928 0.678  1.352  0.042  CBB  AXA 16 
AXA N3   N3   N 0 1 N N N 9.564  -9.165  27.557 0.567  0.070  -0.175 N3   AXA 17 
AXA N4   N4   N 0 1 N N N 11.840 -8.735  27.056 1.887  1.957  0.255  N4   AXA 18 
AXA CBD  CBD  C 0 1 N N N 11.663 -9.295  25.786 3.020  1.225  0.252  CBD  AXA 19 
AXA OAE  OAE  O 0 1 N N N 12.623 -9.356  25.019 4.105  1.748  0.440  OAE  AXA 20 
AXA CBF  CBF  C 0 1 Y N N 10.414 -9.776  25.405 2.908  -0.230 0.013  CBF  AXA 21 
AXA CBC  CBC  C 0 1 Y N N 10.027 -10.269 24.158 3.927  -1.201 -0.039 CBC  AXA 22 
AXA CBE  CBE  C 0 1 Y N N 9.384  -9.701  26.342 1.633  -0.748 -0.199 CBE  AXA 23 
AXA SAT  SAT  S 0 1 Y N N 7.974  -10.302 25.582 1.750  -2.481 -0.466 SAT  AXA 24 
AXA CBA  CBA  C 0 1 Y N N 8.681  -10.624 24.055 3.497  -2.447 -0.278 CBA  AXA 25 
AXA CAJ  CAJ  C 0 1 N N N 8.004  -11.158 22.791 4.398  -3.664 -0.382 CAJ  AXA 26 
AXA CAI  CAI  C 0 1 N N N 8.850  -10.846 21.556 5.760  -3.320 0.226  CAI  AXA 27 
AXA CAK  CAK  C 0 1 N N N 10.293 -11.264 21.842 6.254  -2.000 -0.375 CAK  AXA 28 
AXA CBG  CBG  C 0 1 N N S 10.907 -10.353 22.906 5.397  -0.853 0.162  CBG  AXA 29 
AXA CAN  CAN  C 0 1 N N N 11.069 -8.943  22.332 5.729  0.433  -0.597 CAN  AXA 30 
AXA CAU  CAU  C 0 1 N N N 11.961 -8.922  21.088 6.442  1.391  0.323  CAU  AXA 31 
AXA OAB  OAB  O 0 1 N N N 11.627 -8.297  20.083 6.663  1.075  1.473  OAB  AXA 32 
AXA N5   N5   N 0 1 N N N 13.097 -9.606  21.190 6.833  2.597  -0.133 N5   AXA 33 
AXA HAH  HAH  H 0 1 N N N 9.195  -4.669  32.657 -4.496 1.142  1.660  HAH  AXA 34 
AXA HN1  HN1  H 0 1 N N N 8.785  -2.359  33.222 -6.491 -0.134 2.376  HN1  AXA 35 
AXA HAM  HAM  H 0 1 N N N 8.197  0.390   30.343 -6.919 -2.703 -0.434 HAM  AXA 36 
AXA HAMA HAMA H 0 0 N N N 9.981  -0.208  30.438 -8.656 -2.323 -0.358 HAMA AXA 37 
AXA HAG  HAG  H 0 1 N N N 9.239  -3.362  27.896 -6.028 0.389  -2.971 HAG  AXA 38 
AXA HAF  HAF  H 0 1 N N N 9.552  -5.726  28.529 -4.069 1.814  -2.531 HAF  AXA 39 
AXA HAL  HAL  H 0 1 N N N 10.471 -6.928  31.644 -2.892 3.196  -0.927 HAL  AXA 40 
AXA HALA HALA H 0 0 N N N 8.691  -7.148  31.622 -3.068 2.915  0.822  HALA AXA 41 
AXA HN2  HN2  H 0 1 N N N 8.863  -8.095  29.465 -1.813 0.657  -0.320 HN2  AXA 42 
AXA HN4  HN4  H 0 1 N N N 12.736 -8.390  27.337 1.929  2.914  0.409  HN4  AXA 43 
AXA HAJ  HAJ  H 0 1 N N N 7.884  -12.248 22.880 3.953  -4.495 0.164  HAJ  AXA 44 
AXA HAJA HAJA H 0 0 N N N 7.023  -10.674 22.681 4.523  -3.937 -1.429 HAJA AXA 45 
AXA HAI  HAI  H 0 1 N N N 8.465  -11.403 20.689 5.662  -3.216 1.306  HAI  AXA 46 
AXA HAIA HAIA H 0 0 N N N 8.806  -9.770  21.330 6.472  -4.114 -0.002 HAIA AXA 47 
AXA HAK  HAK  H 0 1 N N N 10.304 -12.302 22.205 7.295  -1.840 -0.094 HAK  AXA 48 
AXA HAKA HAKA H 0 0 N N N 10.881 -11.181 20.916 6.170  -2.040 -1.461 HAKA AXA 49 
AXA HBG  HBG  H 0 1 N N N 11.881 -10.779 23.190 5.597  -0.714 1.225  HBG  AXA 50 
AXA HAN  HAN  H 0 1 N N N 10.075 -8.561  22.056 6.371  0.199  -1.446 HAN  AXA 51 
AXA HANA HANA H 0 0 N N N 11.546 -8.317  23.101 4.807  0.892  -0.955 HANA AXA 52 
AXA HN5  HN5  H 0 1 N N N 13.157 -10.026 22.095 6.656  2.849  -1.052 HN5  AXA 53 
AXA HN5A HN5A H 0 0 N N N 13.787 -9.688  20.471 7.293  3.213  0.459  HN5A AXA 54 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
AXA CAH CAY  DOUB Y N 1  
AXA CAH CAX  SING Y N 2  
AXA CAY N1   SING N N 3  
AXA CAY CAZ  SING N N 4  
AXA N1  CAV  SING Y N 5  
AXA CAV OAC  DOUB N N 6  
AXA CAV CAM  SING N N 7  
AXA CAM OAS  SING N N 8  
AXA OAS CAZ  SING N N 9  
AXA CAZ CAG  DOUB N N 10 
AXA CAG CAF  SING N N 11 
AXA CAF CAX  DOUB N N 12 
AXA CAX CAL  SING N N 13 
AXA CAL N2   SING Y N 14 
AXA N2  CAW  SING Y N 15 
AXA CAW OAD  DOUB N N 16 
AXA CAW CBB  SING Y N 17 
AXA CBB N3   DOUB N N 18 
AXA CBB N4   SING N N 19 
AXA N3  CBE  SING N N 20 
AXA N4  CBD  SING N N 21 
AXA CBD OAE  DOUB N N 22 
AXA CBD CBF  SING N N 23 
AXA CBF CBC  SING N N 24 
AXA CBF CBE  DOUB N N 25 
AXA CBC CBA  DOUB N N 26 
AXA CBC CBG  SING N N 27 
AXA CBE SAT  SING N N 28 
AXA SAT CBA  SING N N 29 
AXA CBA CAJ  SING N N 30 
AXA CAJ CAI  SING N N 31 
AXA CAI CAK  SING N N 32 
AXA CAK CBG  SING N N 33 
AXA CBG CAN  SING Y N 34 
AXA CAN CAU  SING Y N 35 
AXA CAU OAB  DOUB Y N 36 
AXA CAU N5   SING N N 37 
AXA CAH HAH  SING Y N 38 
AXA N1  HN1  SING Y N 39 
AXA CAM HAM  SING N N 40 
AXA CAM HAMA SING N N 41 
AXA CAG HAG  SING N N 42 
AXA CAF HAF  SING N N 43 
AXA CAL HAL  SING N N 44 
AXA CAL HALA SING N N 45 
AXA N2  HN2  SING N N 46 
AXA N4  HN4  SING N N 47 
AXA CAJ HAJ  SING N N 48 
AXA CAJ HAJA SING N N 49 
AXA CAI HAI  SING N N 50 
AXA CAI HAIA SING N N 51 
AXA CAK HAK  SING N N 52 
AXA CAK HAKA SING N N 53 
AXA CBG HBG  SING N N 54 
AXA CAN HAN  SING N N 55 
AXA CAN HANA SING N N 56 
AXA N5  HN5  SING N N 57 
AXA N5  HN5A SING N N 58 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
AXA SMILES           ACDLabs              10.04 O=C1Nc2c(OC1)ccc(c2)CNC(=O)C3=Nc4sc5c(c4C(=O)N3)C(CC(=O)N)CCC5 
AXA InChI            InChI                1.02b 
InChI=1/C22H21N5O5S/c23-15(28)7-11-2-1-3-14-17(11)18-20(30)26-19(27-22(18)33-14)21(31)24-8-10-4-5-13-12(6-10)25-16(29)9-32-13/h4-6,11H,1-3,7-9H2,(H2,23,28)(H,24,31)(H,25,29)(H,26,27,30)/t11-/m0/s1/f/h24-26H,23H2 
AXA InChIKey         InChI                1.02b ITADELAVAWJACR-LKGJLAFSDG 
AXA SMILES_CANONICAL CACTVS               3.341 NC(=O)C[C@@H]1CCCc2sc3N=C(NC(=O)c3c12)C(=O)NCc4ccc5OCC(=O)Nc5c4 
AXA SMILES           CACTVS               3.341 NC(=O)C[CH]1CCCc2sc3N=C(NC(=O)c3c12)C(=O)NCc4ccc5OCC(=O)Nc5c4 
AXA SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1CNC(=O)C3=Nc4c(c5c(s4)CCC[C@H]5CC(=O)N)C(=O)N3)NC(=O)CO2 
AXA SMILES           "OpenEye OEToolkits" 1.5.0 c1cc2c(cc1CNC(=O)C3=Nc4c(c5c(s4)CCCC5CC(=O)N)C(=O)N3)NC(=O)CO2 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
AXA "SYSTEMATIC NAME" ACDLabs              10.04 (5S)-5-(2-amino-2-oxoethyl)-4-oxo-N-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)methyl]-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidine-2-carboxamide 
AXA "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 (5S)-5-(2-amino-2-oxo-ethyl)-4-oxo-N-[(3-oxo-4H-1,4-benzoxazin-6-yl)methyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidine-2-carboxamide           
# 
